Piperidine, 1-Piperoyl

Anderson first hydrolysed piperine by alkalis into a base and an acid, which were named by Babo and Keller piperidine and piperic acid respectively. The chemistry of these products is so well known that it need not be discussed here. The alkaloid was synthesised by Rugheimer by the action of piperoyl chloride on pijieridine. 

The Aedes aegypti (Diptera Culicidae) mosquito is the primary vector in transmitting dengue and yellow fever. Insecticide use has been the primary method of control of this and other mosquitoe species. Piperine [(T,. S )- -piperoyl-piperidine], is the major constituent in Piper nigrum... 

Piperine (1-piperoyl piperidine) in black pepper is shown to possess bioavailabilityenhancing activity with various structurally and therapeutically diverse drugs. This property of piperine may be attributed to increased absorption, which may be due to alteration in membrane lipid dynamics and a change in the conformation of enzymes in the intestine (Khajuria et al., 2002). 

Geisler and Gross (1990) isolated an acyltransferase from shoots of black pepper which catalysed the synthesis of piper-ine in the presence of piperoyl-coenzyme A and piperidine. The enzyme is classified as piperoyl-CoA piperidine IV-piperoyltrans-ferase (piperidine piperoyltransferase EC 2.3.1). 

The main hot component of black pepper is piperine, piperic acid amide or (2E,4E)-piperoyl-l-piperidine or (2 ,4 )-5-(l,3-benzodioxol-5-yl)-N-piperidinylpenta-2,4-dienamide (10-9). Black pepper also contains a number of related compounds as minor components, such as piperanine (10-9) and N-(3,4-methylendioxyphenyl)acylpiperidines with C3, C5, Cy and C9 acyls and the corresponding pyrroHdines, such as piperettine, piperyline, piperoleine A, piperoleine B (10-9) and other compounds. 

The corresponding A -piperideinium cation (41), probably the universal intermediate in piperidine, quinolizidine, and lycopodium alkaloid biosynthesis, is susceptible to nucleophilic attack much like its V-methyl-A -pyrrolinium cation counterpart in pyrrolidine and tropane alkaloid biosynthesis. Moreover, A -piperideine (40) might be reduced to piperidine (42), which now in turn might serve as nucleophilic species. For example, condensation of piperidine (42) with piperoyl-CoA catalyzed by piperidine V-piperoyltransferase (EC 2.3.1.145) yields piperine (43), the main alkaloid found in black pepper where it is responsible for the characteristic pungent taste. 

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